Described are 2,2,3-trimethylcyclopentenyl acetone derivatives defined according to at least one of the structures: ##STR6## as well as processes for making the same, intermediates used in such processes defined according to the structure: ##STR7## and organoleptic uses thereof, particularly uses thereof in augmenting or enhancing the aroma of perfume compositions colognes and perfumed articles.
(Wherein R.sub.3, R.sub.4, and R.sub.5 are the same or different hydrogen or methyl; R.sub.6 represents hydrogen, methyl, ethyl, propyl or isopropyl; x is 0, 1 or 2; R.sub.7 ' and R.sub.7 " represent methyl or ethyl or R.sub.7,(CH.sub.2).sub.x and R.sub.7 " taken together represents C.sub.2 -C.sub.6 alkylene).
Inexpensive, long lasting and intense sweet, green, fruity, pineapple, galbanum and geranium profiles with sweet, fruity, pineapple and green topnotes are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions as well as perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and the like are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Trimethyl substituted cyclopentene acetone derivatives and their alcohol derivatives are known in the art of perfumery. In addition, trimethyl substituted cyclopentene acetone derivatives are known for other uses.
Thus, the compound having the structure: ##STR8## is described by Wawrzenczyk, et al. in Chem. Abstracts Vol. 96, No. 122285 (Abstract of Polish Patent 110257) as having a "fruity odor". Dardzynski, et al. describes the compound having the structure: as having a flowery odor at Chem. Abstracts Vol. 96, No. 122286a (Abstract of Polish Patent 110254). Furthermore, Wawrzenczyk, et al. describes the synthesis of the compound having the structure: ##STR9## at Chem. Abstracts Vol. 101:72956t (Abstract of J. Parkt. Chem. 1984, 326(2), 213-21)
Synthesis of allylic substituted ketone derivatives for the purpose of producing perfumery derivatives is also known as is set forth in Sprecker, et al. U.S. Pat. No. 4,933,320 issued on June 12, 1990 wherein the reaction scheme to wit: ##STR10## is set forth.
Nothing in the prior art, however, describes the 2,2,3-trimethylcyclopentenyl acetone derivatives or infers their organoleptic uses which are unexpected, unobvious and advantageous.